Weaker lewis acid, better catalytic activity: Dual mechanisms in perfluoroarylborane-catalyzed allylstannation reactions

Organic Letters

Volumn 5, Issue 16, 2003, Pages 2857-2860

  Morrison, Darryl J ^a   Piers, Warren E ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BORANE DERIVATIVE; LEWIS ACID;

ALLYLSTANNATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; FLUORINE NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; THERMODYNAMICS;

EID: 0141855245     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034928i     Document Type: Article

References (17)

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3. Lewis acid strength has been shown to directly correlate with reactivity in LA-catalyzed reactions of carbonyls. (a) Ene reactions: Laszlo, P.; Teston-Henry, M. Tetrahedron Lett. 1991, 32, 3837. Laszlo, P.; Teston, M. J. Am. Chem. Soc. 1990, 112, 8750. (b) Aldol reactions: Kobayashi, S. Eur. J. Org. Chem. 1999, 15 and references therein. (c) Classification of LAs on the basis of activity and selectivity: Kobayashi, S.; Tsuyoshi, B.; Nagayama, S. Chem. Eur. J. 2000, 6, 3491.
4. Lewis acid strength has been shown to directly correlate with reactivity in LA-catalyzed reactions of carbonyls. (a) Ene reactions: Laszlo, P.; Teston-Henry, M. Tetrahedron Lett. 1991, 32, 3837. Laszlo, P.; Teston, M. J. Am. Chem. Soc. 1990, 112, 8750. (b) Aldol reactions: Kobayashi, S. Eur. J. Org. Chem. 1999, 15 and references therein. (c) Classification of LAs on the basis of activity and selectivity: Kobayashi, S.; Tsuyoshi, B.; Nagayama, S. Chem. Eur. J. 2000, 6, 3491.
5. Lewis acid strength has been shown to directly correlate with reactivity in LA-catalyzed reactions of carbonyls. (a) Ene reactions: Laszlo, P.; Teston-Henry, M. Tetrahedron Lett. 1991, 32, 3837. Laszlo, P.; Teston, M. J. Am. Chem. Soc. 1990, 112, 8750. (b) Aldol reactions: Kobayashi, S. Eur. J. Org. Chem. 1999, 15 and references therein. (c) Classification of LAs on the basis of activity and selectivity: Kobayashi, S.; Tsuyoshi, B.; Nagayama, S. Chem. Eur. J. 2000, 6, 3491.
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13. + salt, generated separately (see Supporting Information for details).
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